The present invention relates to substituted norbornene ether derivatives of the genus of compounds having the structures: ##STR2## wherein R represents isopropyl.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product.
Long-lasting, fresh, green bean, rosey, citrus, petitgrain-like, fruity, anisic, green, raw potato-like, twiggy, herbaceous, sweet, sweaty, green pea-like, chocolate-like, carrot-like and creamy aroma nuances with galbanum topnotes and anther-like and anise-like undertones are desirable in several types of perfume compositions, perfumed articles and colognes.
The perfume use of norbornene alcohol and ester derivatives having the structures: ##STR3## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl is disclosed in U.S. Pat. No. 3,860,635 particularly at Example XV at column 16 thereof. Such compounds and the synthesis thereof are also disclosed by Bobyleva, Zh. Org. Kh. Volume 13, No. 10, pages 2085-92, October 1977. In addition, ethers of norbornene derivatives having the structures: ##STR4## are disclosed as well as the process for preparing same according to the reaction: ##STR5## in Shields, Can. J. Chem. Volume 49, 1971, page 1142.
U.S. Pat. No. 3,927,116 indicates the utility of certain vinyl norbornyl ethers having the structure: ##STR6## wherein R.sub.2 represents C.sub.1 -C.sub.4 alkyl as being intermediate for the preparation of detergents at column 9 lines 10-15. No indication in U.S. Pat. No. 3,927,116 of the use of such compounds in perfumery, for augmenting or enhancing the aroma of perfumes, perfumed articles and colognes, is suggested either implicitly or explicitly in U.S. Pat. No. 3,297,116.
Sumitomo Chemical Company, Ltd. Japanese Patent No. J74,020,571 published on May 25, 1974 discloses the reaction: ##STR7## wherein R.sup.1 is hydrogen or one to eight carbon alkyl; and R.sup.2 is hydrogen, alkyl or acyl. The Sumitomo Patent indicates that the use of the resultant compounds are as intermediates in the production of medicinal agents and agricultural chemicals. Specifically, the Sumitomo Patent discloses 6-ethoxy-2-isopropylidene norbornane having the structure: ##STR8## No disclosure is set forth in the Sumitomo Patent of the use of the isopropyl ethers of our invention in augmenting or enhancing the aroma of perfumes or augmenting or enhancing organoleptic properties of consumable materials, in general. No disclosure is set forth in the Sumitomo Patent of the use of any of the norbornyl ethers for augmenting or enhancing the aroma or taste of consumable materials.
Thus, the compounds of our invention, having the structures: ##STR9## wherein R is isopropyl have unexpected, unobvious and advantageous perfumery properties over any closely similar compounds of the prior art.